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Issue 32, 2018
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Effect of slight structural changes on the gelation properties of N-phenylstearamide supramolecular gels

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Abstract

Supramolecular gels present several applications in which the gelator properties are closely dependent on their structure and solvent. Despite this, there are few studies on the effect of the gelation ability of gelators with slight molecular changes. Therefore, N-arylestearamides (in which aryl = phenyl (1), 4-tolyl (2) and 4-acetylphenyl (3)) were evaluated in different solvents. The critical gelefication concentration (CGC) values indicated that the substituents can significantly affect the concentration at which the supramolecular gels are formed, mainly in non-aromatic solvents (e.g. cyclohexane, acetonitrile and DMSO). From UV-Vis and DSC data, we verified that the gel–sol and sol–gel transitions (Tgel–sol and Tsol–gel) increase in the order of 1 < 2 < 3. Organogel strength was evaluated for 1–3 as a function of concentration and solvent type using rheology data. Gel strength is concentration-dependent and a strength order was found in acetonitrile, cyclohexane and DMSO, in which: 12 > 3. Dynamic viscoelastic measurements as a function of temperature sweeps indicate a predominantly enthalpic contribution to the elasticity of the organogels formed from 1–3. Temperature-dependent 1H NMR indicates that NH⋯O interactions may be responsible for the molecular association of molecules into 1D fibers, while 3D fibers were formed from van der Waals interactions.

Graphical abstract: Effect of slight structural changes on the gelation properties of N-phenylstearamide supramolecular gels

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Publication details

The article was received on 09 May 2018, accepted on 19 Jul 2018 and first published on 19 Jul 2018


Article type: Paper
DOI: 10.1039/C8SM00961A
Citation: Soft Matter, 2018,14, 6716-6727
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    Effect of slight structural changes on the gelation properties of N-phenylstearamide supramolecular gels

    A. R. Meyer, C. R. Bender, D. M. dos Santos, F. I. Ziembowicz, C. P. Frizzo, M. A. Villetti, J. M. Reichert, N. Zanatta, H. G. Bonacorso and M. A. P. Martins, Soft Matter, 2018, 14, 6716
    DOI: 10.1039/C8SM00961A

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